JP2011026483A - バイオマス由来エポキシ樹脂組成物 - Google Patents
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Abstract
【解決手段】バイオマスのもつフェノール性水酸基やアルコール性水酸基と、酸無水物の有する酸クロを反応させバイオマス由来の酸無水物を新規に合成し、これを硬化剤に用いた。この硬化剤と各種エポキシ樹脂からバイオマス由来エポキシ樹脂組成物を作成した。その硬化物は、耐熱性に優れる。更にエステル構造のため、公知の常圧解重合法によりエポキシ樹脂硬化物は分解され、原料のバイオマスを回収することができる。又、このバイオマスはアルコール性及びフェノール性水酸基を有するため、これをエポキシ樹脂組成物の原料にリサイクルできる。
【選択図】 図1
Description
酸無水物系エポキシ樹脂硬化物の解重合は、特開2005−255835号公報に準拠して行った。
ATMC=無水トリメリット酸クロライド(和光純薬社製)
NMP=N−メチルピロリドン、沸点203℃(和光純薬社製)
AG=無水グルタル酸、融点52℃(和光純薬製)
ESCN=o−クレゾールノボラックエポキシ樹脂 商品名:ESCN−190 エポキシ当量(以下、EEWと略称する)195g/eq(住友化学社製)
Bis A=ビスフェノールA型エポキシ樹脂 商品名:jER828 EEW195g/eq(ジャパンエポキシレジン社製)
Bis F=ビスフェノールF型エポキシ樹脂 商品名:RE404S、EEW165g/eq、(日本化薬社製)
P200=イミダゾール系硬化促進剤 軟化温度97℃(ジャパンエポキシレジン社製)
AL=L由来の酸無水物/LとATMCから得た酸無水物(推定構造第一図) Mw1450
ALP=LP由来の酸無水物/LPとATMCから得た酸無水物 Mw2600
L′=硬化物を解重合して得たL(Mw3200)
LP′=硬化物を解重合して得たLP Mw4600
MEK=メチルエチルケトン(和光純薬社製)
MOE=2−メトキシエタノール(和光純薬社製)
BA=ベンジルアルコール(和光純薬社製)
KBM403=γ−グリシドキシプロピルトリメトキシシラン(信越化学社製)
(1)リグニン由来酸無水物の合成
乾燥した無水トリメリット酸クロライド3.0g(0.0143mol)とNMP10gをフラスコに入れ攪拌した。これに乾燥したL2.0g(HE 107g/eq,0.019mol)を加え溶解後、ピリジン1.2g(0.015mol)を20分かけて加える。滴下終了後、液温20℃で8時間攪拌した。その後、減圧ろ過して、ピリジン塩酸塩を除き、酸無水物はエステルを介して付加したL(以下、ALと略称する)を得た。推定構造式を図1に示す。
(2)エポキシ樹脂組成物の硬化
エポキシ樹脂としてEL(EEW380g/eq)を2gと実施例1で得たALを化学量論比で配合し、硬化促進剤P200を樹脂分の2wt%加え樹脂ワニスを作製し、ポリイミドフィルム上に塗布して、熱硬化し厚さ100〜200μmのエポキシ樹脂硬化フィルムを得た。硬化条件は60℃/1h+120℃/1h/160℃/1h+200℃/1hであった。
実施例1に準拠して作成した、実施例2〜実施例8の硬化物のガラス転移温度を測定した。なお、実施例7と実施例8のエポキシ樹脂は二成分混合系であり、これらは等モルの配合である。その結果を表1に併記するようにガラス転移温度は210〜185℃であった。
実施例9は実施例1で用いたエポキシ樹脂硬化物を処理液で分解し、原料のLを得た。
実施例9に準拠してLPを得た。そのHEは180g/eq、Mw4500であった。これを硬化剤に用い、実施例10のエポキシ樹脂組成物及び硬化物を得た。そのガラス展温度は175℃であった。本発明のバイオマス由来酸無水物を用いたエポキシ樹脂硬化物を解重合して得たバイオマスを硬化剤に用いることができることが分かった。
バイオマス由来の酸無水物であるAGを硬化剤に用いた場合のエポキシ樹脂組成物及びその硬化物のガラス転移温度を表1に併記した。ガラス転移温度は130〜153℃であり、本発明のバイオマス由来の酸無水物である、実施例で示したALやALPを用いた硬化物に比べ、ガラス転移温度は低いことが明らかである。
表1に示す実施例1の組成物にMEK/MOE(溶媒量等量)を加えNV(固形分濃度)50%のワニスを得た。
Bis F 80gと、ELを20gと、硬化剤としてAL 40gにカップリング材としてKBM403を4.2gとフィラー:高純度球状フィラーである次の3種類(混合比a/0.6:b/0.3:c/0.1)を用い、混合物を上記樹脂に対して50v%加えた。
a:SP−4B、平均粒径5.1μm(扶桑化学社製)
s:QS4F2、平均粒径4.6μm、SO25R(三菱レーヨン社製)
c:SO25R、平均粒径0.68μm(龍森社製)。
2 金メッキ
3 金バンプ
4 半導体素子
5 はんだボール
6 エポキシ樹脂硬化物
Claims (11)
- エポキシ樹脂と、硬化剤とを含むバイオマス由来エポキシ樹脂組成物であって、前記硬化剤が、重量平均分子量が300〜5000のバイオマスに、エステル基を介して酸無水物を付加したバイオマス由来酸無水物であることを特徴するバイオマス由来エポキシ樹脂組成物。
- 前記バイオマスが、低分子リグニン,リグノフェノール,タンニン及びクラフトリグニンから選ばれる少なくとも1種であることを特徴とする請求項1記載のバイオマス由来エポキシ樹脂組成物。
- 前記酸無水物が、酸クロやカルボキシルを有することを特徴とする請求項1または2記載のバイオマス由来エポキシ樹脂組成物。
- 前記エポキシ樹脂が、バイオマスにエポキシ基を付加したバイオマス由来エポキシ樹脂,石油由来エポキシ樹脂の少なくとも一方であることを特徴とする請求項1に記載のバイオマス由来エポキシ樹脂組成物。
- 硬化後のガラス転移温度が、150℃以上であることを特徴とする請求項1乃至4のいずれか1項に記載のバイオマス由来エポキシ樹脂組成物。
- 請求項1記載のバイオマス由来エポキシ樹脂組成物と、このエポキシ樹脂組成物を溶解するための溶媒とを含み、そのエポキシ樹脂組成物の濃度が0.5〜95%であることを特徴とするワニス。
- 請求項6に記載のワニスを基材に含浸させ、乾燥して作製したことを特徴とするプリプレグ。
- 請求項7記載のプリプレグを用いたことを特徴とするプリント配線板。
- 請求項7記載のプリプレグを用いたことを特徴とする電子機器。
- 請求項7記載のプリプレグを用いたことを特徴とする回転電機。
- 請求項5記載のバイオマス由来エポキシ樹脂組成物の硬化物を解重合し、回収したバイオマスを再度、硬化剤及び/またはエポキシ樹脂に変性することを特徴とするバイオマス由来エポキシ樹脂組成物の製造方法。
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JP2009174885A JP5244728B2 (ja) | 2009-07-28 | 2009-07-28 | バイオマス由来エポキシ樹脂組成物 |
US12/843,979 US8420766B2 (en) | 2009-07-28 | 2010-07-27 | Biomass-derived epoxy resin composition |
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US8664305B2 (en) * | 2009-02-10 | 2014-03-04 | The Goodyear Tire & Rubber Company | Functionalized lignin, rubber containing functionalized lignin and products containing such rubber composition |
JP2010241855A (ja) * | 2009-04-01 | 2010-10-28 | Hitachi Ltd | エポキシ樹脂組成物 |
JP2011075927A (ja) * | 2009-09-30 | 2011-04-14 | Fujifilm Corp | 光学フィルムとその製造方法、偏光板、光学補償フィルムおよび液晶表示装置 |
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JP2010163497A (ja) * | 2009-01-13 | 2010-07-29 | Toshiba Corp | 高分子組成材料およびその製造方法 |
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KR101561980B1 (ko) * | 2014-01-03 | 2015-10-20 | 주식회사 에스아이켐 | 환경호르몬을 배출하지 않는 바이오에폭시 수지의 제조방법 |
US10968329B2 (en) * | 2016-03-08 | 2021-04-06 | Showa Denko Materials Co., Ltd. | Method of recovering decomposition product of thermosetting resin cured product and method of producing recycled material |
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JP5244728B2 (ja) | 2013-07-24 |
US8420766B2 (en) | 2013-04-16 |
US20110024168A1 (en) | 2011-02-03 |
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